If you are set on buying a multi family property and want your own space you might have to look a little further out then your home town if you want to stay in Kentucky I would recommend bowling green the area is really growing and has a growing college in town as well hope this helps and good luck!

@Evan Alexakos, I am impressed that you have saved $20k while in college. 

It's relatively close to the local college.

It’s a D1 college town actually.

I may also potentially need to use some student loans to acquire my master’s degree.

I suppose you can use something like Mint to automate input to some degree.

Although I don't invest in any STR's, a few friends do and they've been pretty happy with the degree of management they've had to do with their investments.

College towns tend to be excellent markets for both appreciation and cash flow so it might be a good idea to hold on to this property especially if you are close to the university.

However, how (to what degree) does the cost of capital fit into the picture or does it? 

Look for specific courses at a college or on the job training.